Flightline Associates is a boutique advisory firm based in Seattle and London. We work with leadership teams facing regulatory scrutiny, board oversight, or investor diligence. We've run operations ourselves, so we advise like operators.
CEO and founder, Seattle and London
Richard has spent 30 years in the rooms where technology, finance, and operating complexity collide. He was on the original AOL team that turned spare data center capacity into what is now called the cloud. At Microsoft, he was accountable for the profitability of every cloud product, from Azure to Xbox Live, with a P&L of more than USD 40 billion. At JPMorgan Chase, he was CFO for global technology infrastructure and a founding member of the bank's Alternative Energy working group.
He has led teams of more than 1,000 people, raised more than USD 4 billion in capital, overseen the buildout of more than 300 data centers, and led the integration of several major M&A deals. He has done it on four continents and in 55 countries, under the kind of scrutiny where one missed detail becomes a headline.
He founded Flightline for the engagements nobody else wants: complex, politically sensitive, or already drifting. His approach hasn't changed in three decades. Make the most of technology, stay fiscally disciplined, focus on operations, and manage risk. And yes, he's a pilot. The name is no accident.
“I work with enterprise leaders when technology, finance, and operating complexity collide, and failure is not an option.”
Microsoft · JPMorgan Chase · AOL · Tata Communications · Lumen · CORTAC Group
MBA, UNC Kenan-Flagler (OneMBA) · BSBA, The Ohio State University · Professional Engineer (P.E.) · Certified Treasury Professional (CTP) · Oxford Saïd AI program
DataRoomed · BrandHat · Shuffle · UnderscoreWork · GetTrooth · Northwest Association for Financial Professionals
Chief Revenue Officer, UnderscoreWork and GetTrooth · Angel investor and incubator · Co-director, Startup Grind Seattle
Three commitments guide every engagement, from the first discovery call to the final progress report.
We're independent of vendors, platforms, and service providers. Our recommendations serve your organization's interests, not sales quotas or referral arrangements.
Our experience comes from regulated industries, government contractors, and organizations under regulatory scrutiny. We understand compliance requirements, audit processes, and board expectations.
Our work is designed to be implemented and to hold up under scrutiny. Outcomes over presentations, execution over slideware, accountability over opinion.
We work with proven frameworks and trusted delivery partners instead of building everything from scratch.
We deliver infrastructure and technology investment decisions with Apptio and NimbusStack, and we're active members of the TBM Council in North America and EMEA.
Leadership coaching for teams through AI implementation and organizational change.
A partner ecosystem that connects portfolio companies with professional services, delivery partners, and secondary market opportunities.
Our partners extend what we can deliver. They never decide what we recommend.
